Cheap Flights from Milan to Chicago, IL from $352

Return flight: Chicago – Milan

On Cheapflightsplus.com you will find 229 connecting flights from Milan to Chicago. You can compare airfare deals from 26 airlines and multiple travel sites from $352, book and save on cheap plane tickets and last minute offers. Also check out MIL-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Milan to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $352 (one-way), $604 (round-trip).
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Full flight schedule will help you in detecting at what time planes fly from Milan to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
Departure Arrival Flight Details Flight Duration Price
06:20 — 15:30
06:20 — 08:15 TP829 TAP Portugal
Milan — Lisbon
3h 45m stop
11:55 — 15:30 TP243 TAP Portugal
Lisbon — Chicago
16h 10m
including layover
Find flight
from$488
06:25 — 13:25
06:25 — 07:45 UA9305 United Airlines
Milan — Frankfurt
3h 5m stop
10:50 — 13:25 UA8836 United Airlines
Frankfurt — Chicago
14h
including layover
Find flight
from$789
07:00 — 10:10
+1 day
07:00 — 12:00 TK1878 Turkish Airlines
Milan — Istanbul
19h 35m stop
07:35 — 10:10 TK185 Turkish Airlines
Istanbul — Chicago
34h 10m
including layover
Find flight
from$531
07:15 — 17:20
07:15 — 10:50 U23969 EasyJet
Milan — Reykjavik
5h 55m stop
16:45 — 17:20 FI853 Icelandair
Reykjavik — Chicago
17h 5m
including layover
Find flight
from$590
09:10 — 15:15
09:10 — 10:35 UA9081 United Airlines
Milan — Frankfurt
2h 15m stop
12:50 — 15:15 UA906 United Airlines
Frankfurt — Chicago
13h 5m
including layover
Find flight
from$786
09:50 — 18:25
09:50 — 11:00 LH7405 Lufthansa
Milan — Munich
4h 35m stop
15:35 — 18:25 LH434 Lufthansa
Munich — Chicago
15h 35m
including layover
Find flight
from$1438
10:40 — 16:15
10:40 — 11:45 LX1613 SWISS International Air Lines
Milan — Zurich
1h 25m stop
13:10 — 16:15 LX8 SWISS International Air Lines
Zurich — Chicago
12h 35m
including layover
Find flight
from$1436
10:40 — 12:55
+1 day
10:40 — 11:45 LX1613 SWISS International Air Lines
Milan — Zurich
21h 55m stop
09:40 — 12:55 LX3204 SWISS International Air Lines
Zurich — Chicago
33h 15m
including layover
Find flight
from$1467
11:30 — 18:45
11:20 — 12:30 BA565 British Airways
Milan — London
3h 5m stop
15:45 — 18:45 BA297 British Airways
London — Chicago
14h 15m
including layover
Find flight
from$927
11:30 — 16:50
11:20 — 12:30 BA565 British Airways
Milan — London
1h 30m stop
14:10 — 17:00 BA1542 British Airways
London — Chicago
12h 20m
including layover
Find flight
from$944
12:10 — 12:15
+1 day
12:10 — 13:45 SN3148 Brussels Airlines
Milan — Brussels
20h 25m stop
10:10 — 12:15 SN8803 Brussels Airlines
Brussels — Chicago
31h 5m
including layover
Find flight
from$1481
12:20 — 14:55
+1 day
12:20 — 21:35 EK2141 Emirates
Milan — Dubai
12h 10m stop
09:45 — 14:55 EK235 Emirates
Dubai — Chicago
33h 35m
including layover
Find flight
from$1473
13:15 — 18:25
13:15 — 14:25 LH9449 Lufthansa
Milan — Munich
1h 10m stop
15:35 — 18:25 LH434 Lufthansa
Munich — Chicago
12h 10m
including layover
Find flight
from$1436
14:15 — 16:50
+1 day
14:10 — 15:15 BA589 British Airways
Milan — London
22h 50m stop
14:10 — 17:00 BA1542 British Airways
London — Chicago
33h 35m
including layover
Find flight
from$944
14:30 — 13:25
+1 day
14:30 — 15:55 LH5637 Lufthansa
Milan — Frankfurt
18h 55m stop
10:50 — 13:25 LH430 Lufthansa
Frankfurt — Chicago
29h 55m
including layover
Find flight
from$1453
15:15 — 15:15
+1 day
15:15 — 21:30 RJ104 Royal Jordanian
Milan — Amman
13h 5m stop
10:35 — 15:15 RJ263 Royal Jordanian
Amman — Chicago
31h
including layover
Find flight
from$696
15:50 — 16:50
+1 day
15:30 — 16:40 BA591 British Airways
Milan — London
21h 10m stop
14:10 — 17:00 BA1542 British Airways
London — Chicago
32h
including layover
Find flight
from$943
16:50 — 16:50
+1 day
16:35 — 17:40 BA575 British Airways
Milan — London
20h 15m stop
14:10 — 17:00 BA1542 British Airways
London — Chicago
31h
including layover
Find flight
from$944
16:50 — 13:55
+1 day
16:35 — 17:40 BA575 British Airways
Milan — London
17h 5m stop
11:00 — 13:55 BA295 British Airways
London — Chicago
28h 5m
including layover
Find flight
from$946
17:20 — 18:25
+1 day
17:20 — 18:30 LH1857 Lufthansa
Milan — Munich
21h 5m stop
15:35 — 18:25 LH434 Lufthansa
Munich — Chicago
32h 5m
including layover
Find flight
from$1445
17:20 — 14:10
+1 day
17:20 — 18:30 LH1857 Lufthansa
Milan — Munich
16h 55m stop
11:25 — 14:10 LH9268 Lufthansa
Munich — Chicago
27h 50m
including layover
Find flight
from$1476
18:35 — 10:10
+1 day
18:35 — 23:35 TK1876 Turkish Airlines
Milan — Istanbul
8h stop
07:35 — 10:10 TK185 Turkish Airlines
Istanbul — Chicago
22h 35m
including layover
Find flight
from$531
18:55 — 13:55
+1 day
18:55 — 19:55 BA569 British Airways
Milan — London
15h 5m stop
11:00 — 13:55 BA295 British Airways
London — Chicago
26h
including layover
Find flight
from$927
19:10 — 14:30
+1 day
19:10 — 21:30 IB676 Iberia
Milan — Madrid
14h 5m stop
11:35 — 14:30 AY5659 Finnair
Madrid — Chicago
26h 20m
including layover
Find flight
from$948
19:45 — 20:00
+1 day
19:30 — 21:40 LO320 LOT
Milan — Warsaw
18h 45m stop
16:40 — 20:00 LO3 LOT
Warsaw — Chicago
31h 15m
including layover
Find flight
from$850
20:00 — 15:50
+1 day
20:00 — 22:05 SK688 SAS
Milan — Copenhagen
15h 15m stop
13:35 — 15:50 SK943 SAS
Copenhagen — Chicago
26h 50m
including layover
Find flight
from$685
20:15 — 15:50
+1 day
20:15 — 22:25 U23925 EasyJet
Milan — Copenhagen
14h 55m stop
13:35 — 15:50 SK943 SAS
Copenhagen — Chicago
26h 35m
including layover
Find flight
from$621
21:55 — 12:15
+1 day
21:55 — 23:25 SN3160 Brussels Airlines
Milan — Brussels
10h 45m stop
10:10 — 12:15 SN8803 Brussels Airlines
Brussels — Chicago
21h 20m
including layover
Find flight
from$1480
*Departure and arrival times - local. Updated on February 16, 2025

Flight Information

Below we will explain in detail what the flights cost on the destination from Milan to Chicago depends on and how to choose the most interesting flight option for you.

Distance between Milan and Chicago is 7289 miles. Time difference between the cities is 7h. Airplanes depart 06:10 to 22:35 from 4 Milan airports and arrive 06:10 to 22:35 to 7 Chicago airports. Average flight time is 26h 25m.

  • The fastest flight 12h 10m
  • Average flight time 26h 25m
  • The earliest flight 06:10
  • The latest flight 22:35
  • Distance 4530 ml

The cheapest months to travel to Chicago are february (from 352 $), january (from 379 $), november (from 488 $).

The most expensive months are december (from 488 $), november (from 488 $), january (from 379 $).

What is the lowest airfare Milan to Chicago?

The cheapest plane ticket found by our users is $352. This airfare is for economy class on one-way U23969 flight by EasyJet for February 21, 2025 which leaves Malpensa in Milan at 07:15 am and arrives at Chicago Midway at 20:08.

Economy class
$352
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Business class
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First class
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Popular Airlines on the Route

The flight Milan — Chicago is served by 26 regular airlines and 4 low-cost airlines. Most of the flights on this route are operated by United Airlines - 4 departures per week at the price of from $ 786 . And the most expensive tickets are offered by Air Dolomiti airline - from $ 2698.

Direct flights

There’re no direct flights on this route. Try flights with stops.

Connecting Flights

There are 229 flights with layovers on the route. The fastest connecting flight is LH9449 by Lufthansa takes 12h 10m and the cheapest is U23969 by EasyJet for $352.

See more connecting flights

Airports

You can fly from Milan to Chicago from 4 airports (Linate, Malpensa, Milan Bergamo (Orio al Serio), Segrate).

Milan airports

  • Linate-LIN
    from $382
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  • Malpensa-MXP
    from $352
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  • Milan Bergamo (Orio al Serio)-BGY
    from $613
    Find
  • Segrate-SWK
    Find

Chicago airports

  • O'Hare International-ORD
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  • Midway-MDW
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  • Dupage County-DPA
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  • Chicago FSS-CHI
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  • Merrill C Meigs (closed)-CGX
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  • Pal-Waukee-PWK
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  • Chicago NAS-NOH
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How to book a plane ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

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